Post # 1
I recently found an amazing deal on airfare to Chicago. Fiance and I canceled a flight a while back, so we could use those points and fly to Chicago for $20 round trip! Fiance is a huge Cubs fan, and he’s never been to Chicago so I’d love to take him to see a Cubs game! We’d probably do 2 days – fly in morning one day, and leave afternoon/night the next day. Does anyone have recommendations on what to do in the Chicago area besides seeing a baseball game? Also, if anyone has affordable hotel recommendations that are near Wrigley Field (or easy to get to on the train), that would be greatly appreciated! Thanks!
Post # 2
Some of the more touristy things to do might be a visit to Navy Pier, the sky deck, walking the mag mile or dinner at the Signature Room.
Less touristy would be biking the lake path/606, a day at the beach, checking out parks. It sounds like you’re coming during the summer and good for you because we take our summers very seriously. There is a 100% percent chance that there will be a music festival, block party, art show, other outdoor event going on while you’re here. Just google “Chicago festivals [your dates]. Also, get to Wrigleyville early, start drinking at the nearby bars and just start asking people what’s going on later. They’ll tell you, and sometimes it’s more fun to not have a plan anyway.
My biggest piece of advice is to get out of the touristy, high traffic areas like downtown, River North, and Lakeview and try to get to some of the actual neighborhoods where real people live. You will see more of the City, make great “vacation friends,” and get some street cred for having done something besides take a selfie with the Bean.
Also, come hungry. Eat everything.
Post # 3
Definitely do an architectural boat tour. I have lived in the city for 14 years and I do at least one every summer. Best way to see the city!
Post # 4
Make sure it’s the tour given by the Chicago Architecture Foundation. Its the best one by far.
Post # 5
kgr9 : Yes! I always push people to see how Chicagoans actually like. I work downtown but definitely do not spend all of my time there.
OP: Wrigleyville is a great place! You guys will love everything about it. I would suggest using Priceline (or one of those sites) for a better deal (we use Express Deals). You can get a decent hotel that way. I agree with previous posts about the touristy spots. Drink, eat, and shop your way through the city. It’s a great way to see everything.